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Cyclobutanecarboxylic acid

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CAS#[3721-95-7]

G-codeGEO-00852

EC number223-072-7

Molecular formulaC₅H₈O₂

Molecular weight100.12

General description and preparation

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Regulatory Information

Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.

Product categorization

Main category

Carboxylic acids / salts

Second level

Aliphatic compounds

Description

Cyclobutanecarboxylic acid is a useful chemical compound with a variety of research applications. We are pleased to offer high quality Cyclobutanecarboxylic acid in various sizes (for research, pilot-scale, or production applications) from milligrams to multi-kilogram batches, making it easy for you to choose the right amount to suit your needs.

Cyclobutanecarboxylic acid is useful principal reagent for the preparation of various monosubstituted cyclobutane derivatives in the synthesis of biological…

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General description of Cyclobutanecarboxylic acid

Cyclobutanecarboxylic acid or cyclobutyl formic acid [3721-95-7] is a colorless liquid with the boiling point of 196 °C^[1] at atmospheric pressure and melting point around -7 °C^[2]. Altought relatively high LD50 (mouse, subcutaneous and intraperitoneal, 1270 mg/kg),^[3] this compound is corrosive and can cause severe skin burns and eye damage. Cyclobutanecarboxylic acid is usually prepared by the hydrolysis and decarboxylation of diethyl cyclobutanedicarboxylate, formed in reaction of trimethylene dibromide with ethyl malonate and sodium in ethanol.^[4] Another preparation is based on the oxidative ring contraction of cyclopentanone with hydrogen peroxide catalysed with selenium dioxide.^[5]

Application of Cyclobutanecarboxylic acid

Cyclobutanecarboxylic acid is useful principal reagent for the preparation of various monosubstituted cyclobutane derivatives in the synthesis of biological active compounds and approved drugs as Butorphanol^[6], Nalbuphine^[7], Boceprevir^[8] and others.^[9]

Notes

Stable under recommended storage conditions. Conditions to avoid: Heat, flames and sparks. Incompatible materials: Strong oxidizing agents, Strong bases

Product categorization (Chemical groups)

Main category:

Carboxylic acids / salts

Second level:

Aliphatic

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[1] G. H. Jeffery, A. I. Vogel Ruter J. Chem. Soc. 1948, 1804. [2] J. Boeseken, A. G. Lutgerhorst Recl. Trav. Chim. Pays-Bas 1932, 75, 1846. [3] A. E. Senior, H. S. Sherratt, J. Pharm. Pharmac. 1969, 85. [4] Org. Synth. 1943, 23, 16. Cason, Ch. F. Allen J. Org. Chem. 1949, 14, 1036. [5] G. B. Payne, C. W. Smith J. Org. Chem. 1957, 22, 1680. [6] I. Monković, H. Wong, A. W. Pircio, Y. G. Perron, I. J. Pachter, B. Belleau Can. J. Chem. 1975, 53, 3094. [7] R.S. Vardanyan, V.J. Hruby Synthesis of Essential Drugs 2006, Elsevier. [8] D. S. Bhalerao, A. K. R. Arkala, Y. V. Madhavi, M. Nagaraju, S. R. Gade, U K. S. Kumar, R. Bandichhor, V. H. Dahanukar Org. Process Res. Dev. 2015, 19, 1559. [9] A. Sergeiko, V. V. Poroikov, L. O. Hanuš, V. M. Dembitsky Open Med. Chem. J. 2008, 2, 26.</div<

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